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AB141023

9-cis-Retinoic acid, Endogenous retinoic acid receptor agonist

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(2 Publications )

MW 300.4 Da, Purity >98%. High affinity, endogenous retinoic acid receptor (RAR) agonist (IC50= 14 nM for RARα, RARβ and RARγ). Active metabolite of vitamin A. Acts as a transcription factor to regulate the growth and differentiation of normal and malignant cells and capable of inhibiting prostaglandin-endoperoxide synthase 2 expression.

View Alternative Names

Atherosclerosis, susceptibility to, included, DAUD I6, DKFZp686N23123, ER, ER-alpha, ER-beta, ER[a], ER[b], ESR, ESR B, ESR BETA, ESR1_HUMAN, ESRA, ESTR B, Early response protein NAK1, Era, Erb, Erb2, Estr, Estra, Estradiol Receptor alpha, Estradiol Receptor beta, Estradiol receptor, Estrogen Receptor 1, Estrogen Receptor 2, Estrogen receptor, Estrogen receptor 1 (alpha), Estrogen receptor 2 (ER beta), Estrogen receptor 2 ER beta, Estrogen receptor alpha, Estrogen receptor beta 4, Estrogen resistance, included, FLJ00280, FLJ00318, FLJ16020, FLJ16733, GFRP 1, Growth Factor Inducible Nuclear Protein NP10, Growth Factor Response Protein 1, Growth factor inducible nuclear protein N10, H 2RIIBP, HAP, HBV-activated protein, HDL cholesterol, augmented response of, to hormone replacement, included, HMR, Hbr1, Hormone Receptor, LX receptor beta, LXR a, LXR b, LXR beta, Liver X nuclear receptor beta, Liver X receptor alpha, Liver X receptor beta, MGC102720, MGC109416, MGC1831, MGC9485, MHC class I promoter binding protein, Myocardial infarction, susceptibility to, included, N10, N10 nuclear protein, NAK 1, NER I, NER1, NGFIB, NP 10, NR1B1, NR1B2, NR1B3, NR1H2_HUMAN, NR1H3_HUMAN, NR2B1, NR2B2, NR2B3, NR3A1, NR3A2, NR4A1_HUMAN, NUR77, mouse, homolog of, Nerve growth factor IB nuclear receptor variant 1, Nuclear Hormone Receptor TR3, Nuclear hormone receptor NUR/77, Nuclear mitotic apparatus protein retinoic acid receptor alpha fusion protein, Nuclear orphan receptor LXR beta, Nuclear receptor NER, Nuclear receptor subfamily 1 group B member 1, Nuclear receptor subfamily 1 group B member 2, Nuclear receptor subfamily 1 group B member 3, Nuclear receptor subfamily 1 group H member 2, Nuclear receptor subfamily 1 group H member 3, Nuclear receptor subfamily 2 group B member 1, Nuclear receptor subfamily 2 group B member 2, Nuclear receptor subfamily 2 group B member 3, Nuclear receptor subfamily 3 group A member 1, Nuclear receptor subfamily 3 group A member 2, Nuclear receptor subfamily 4 group A member 1, Nucleophosmin retinoic acid receptor alpha fusion protein NPM RAR long form, OR-1, OTTHUMP00000017718, OTTHUMP00000017719, OTTHUMP00000022510, OTTHUMP00000060418, Orphan nuclear receptor HMR, Orphan nuclear receptor NR4A1, Orphan nuclear receptor TR3, Orphan receptor tr3, Oxysterols receptor LXR-alpha, Oxysterols receptor LXR-beta, RAR, RAR-alpha, RAR-beta, RAR-epsilon, RAR-gamma, RARA_HUMAN, RARB_HUMAN, RARC, RARG_HUMAN, RARalpha1, RIP15, RLD 1, RNESTROR, RRB2, RXR alpha1, RXR beta, RXR gamma, RXRA_HUMAN, RXRB_HUMAN, RXRC, RXRG_HUMAN, Receptor NGFIB, Retanoic X receptor gamma, Retinoic acid nuclear receptor alpha variant 1, Retinoic acid nuclear receptor alpha variant 2, Retinoic acid receptor RXR-alpha, Retinoic acid receptor RXR-beta, Retinoic acid receptor RXR-gamma, Retinoic acid receptor alpha, Retinoic acid receptor alpha polypeptide, Retinoic acid receptor beta, Retinoic acid receptor beta 2, Retinoic acid receptor beta 4, Retinoic acid receptor beta 5, Retinoic acid receptor beta polypeptide, Retinoic acid receptor gamma 2, Retinoic acid receptor, gamma, Retinoid X nuclear receptor alpha, Retinoid X receptor alpha, Retinoid X receptor beta, Retinoid X receptor gamma, ST-59, Steroid hormone nuclear receptor NER, Steroid receptor TR3, TR 3, TR3 orphan receptor, Testicular receptor 3, UNR, Ubiquitously-expressed nuclear receptor

1 Images
Chemical Structure - 9-cis-Retinoic acid, Endogenous retinoic acid receptor agonist (AB141023)
  • Chemical Structure

Lab

Chemical Structure - 9-cis-Retinoic acid, Endogenous retinoic acid receptor agonist (AB141023)

2D chemical structure image of ab141023, 9-cis-Retinoic acid, Endogenous retinoic acid receptor agonist

Key facts

CAS number

5300-03-8

Purity

>98%

Form

Solid

form

Molecular weight

300.4 Da

Molecular formula

C<sub>2</sub><sub>0</sub>H<sub>2</sub><sub>8</sub>O<sub>2</sub>

PubChem

449171

Nature

Synthetic

Solubility

Soluble in DMSO to 25 mM

Soluble in ethanol to 25 mM

Biochemical name

Alitretinoin

Biological description

High affinity, endogenous retinoic acid receptor (RAR) agonist (IC50= 14 nM for RARα, RARβ and RARγ). Active metabolite of vitamin A. Acts as a transcription factor to regulate the growth and differentiation of normal and malignant cells and capable of inhibiting prostaglandin-endoperoxide synthase 2 expression.

Canonical smiles

CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C

Isomeric smiles

CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\C(=O)O)\C)/C

InChi

InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+

InChiKey

SHGAZHPCJJPHSC-ZVCIMWCZSA-N

IUPAC Name

(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
-20°C
Appropriate long-term storage conditions
-20°C
Storage information
It is important to note that this product is reported to be light sensitive|Store in the dark|Store under desiccating conditions|The product can be stored for up to 12 months
Handling instructions

Need more advice on solubility, usage and handling? Please visit our our product support page for more details.

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Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

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Toxic, refer to SDS for further information.

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

The retinoic acid receptors and retinoid X receptors are part of a larger family of nuclear receptors that play main roles in gene expression. Retinoic acid receptor gamma (RARγ) NUR77 estrogen receptor (ER) LXR alpha (liver X receptor alpha) RXRG RAR alpha RAR beta RXRB RXRA and LXR beta are alternate names of these proteins. Masses of these proteins vary with RXRA for example around 55 kDa. These receptors are expressed in various tissues including the liver bone marrow and adipose tissue demonstrating broad physiological relevance.
Biological function summary

Retinoic acid receptors function by binding to retinoic acid and this binding influences gene transcription. Usually they form heterodimers with retinoid X receptors to perform their function more effectively. This complex modulates expression of genes involved in cell differentiation apoptosis and lipid metabolism. RAR and RXR proteins also interact with other nuclear receptors further influencing the regulation of key metabolic processes.

Pathways

Retinoic acid receptors and retinoid X receptors are critical in the retinoic acid signaling pathway and lipid metabolism pathways. In these pathways they closely associate with proteins such as PPARs (peroxisome proliferator-activated receptors) to coordinate regulation of genes linked to energy homeostasis. These specific interactions ensure the maintenance of normal cellular functions and contribute to the body's ability to adapt to nutritional and metabolic changes.

Disruptions in retinoic acid receptor and retinoid X receptor functions link to cancer and metabolic syndrome. Specifically abnormal expression or mutations in these receptors can drive the progression of acute promyelocytic leukemia and non-alcoholic fatty liver disease. The involvement of related proteins such as PPARs in these pathways further implicates the importance of maintaining proper function and regulation of these receptor families in disease prevention and management.

Product protocols

Publications (2)

Recent publications for all applications. Explore the full list and refine your search

Communications biology 7:1532 PubMed39604738

2024

Proximal tubule cell maturation rate and function are controlled by PPARα signaling in kidney organoids.

Applications

Unspecified application

Species

Unspecified reactive species

Yoshiki Sahara,Chie Fukui,Yuki Kuniyoshi,Minoru Takasato

Aging 12:5469-5478 PubMed32209731

2020

Intranasal delivery of 9-cis retinoic acid reduces beta-amyloid deposition via inhibiting astrocyte-mediated inflammation.

Applications

Unspecified application

Species

Unspecified reactive species

Hong Zhao,Shuo Li,Zhuo Li,Shuo Yang,Dandan Li,Jiaolin Zheng,Hongmei Gao,Ling Yun,YingLi Gu,Longxuan Li,Jing Zhao,Yuan Fu
View all publications

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